To call them “million dollar” views may be a significant case of under-valuation. From the home’s multitude of decks, you can gaze out across to San Francisco, to Sausalito, towering Mount Tamalpais and the Golden Gate Bridge in the distance. The sunsets are beyond epic.
Venture capitalist Todd Chaffee snapped up the seaside lot on Belvedere Island, on the north side of San Francisco Bay in 2000. And he proceeded to spend five years and a reported $25 million, building his 7,000-square-foot dream home.
Chaffee, 60, who’s advisory partner at investment powerhouse Institutional Venture Partners, is known for his savvy investments in tech sweethearts like Netflix, Kayak and Pandora. His $44 million early bet on Twitter ultimately turned into a return of close to $5 billion for his company, according to Forbes.
Before landing on this perfect spot, Chaffee lived in three different properties on elite Belvedere Island.
Linked by two causeways to Tiberon, the island measures just one mile around, and was first developed in the late 1890s as a weekend getaway for rich San Franciscans. Today it has just 2,100 residents and is said to be the eighth highest-income community in the US.

Todd Chaffee’s Bay Area home on Belvedere Island. Photo: Matt McCourtney
“The magic of Belvedere Island is that it’s an unbelievable place and a world-class location,” Chaffee recently told Bloomberg. “The luxury of it is I can pop to the city for meetings, pop up to wine country, or I’m two minutes away from going sailing.”

The modern entrance seems modest, but the home is 7,000 square feet. Photo: Matt McCourtney
Clinging to a cliff face on the west side of Belvedere, the sleek, ultra-modern, indoor-outdoor home was designed by awarding-winning San Francisco architects Aidlin Darling Design to make the most of the views.
Open the front door from the home’s expansive motorcourt, and all you see is an expanse of water through the floor-to-ceiling glass. Steps lead down to the main level with its formal dining area and living spaces, along with three bedrooms, a gym and sundeck.

The kitchen. Photo: Matt McCourtney
Huge pocket doors slide into the wall to the open the dining room and kitchen to a vast water-front deck. On this level, there’s also a media room and art studio, plus a cozy interior courtyard with covered dining table and firepit seating.

The open dining room. Photo: Matt McCourtney
Upstairs on the entry level is a master suite the listing describes as one “worthy of a five-star resort.” Floor to ceiling glass windows lead on to a huge terrace with uninterrupted views across to Sausalito.

The resort-worthy master suite. Photo: Matt McCourtney
If there’s a need to do a quick check of your stock portfolio, on this level there’s a spacious custom office, with a second one close by. One has been used as Chaffee’s retreat, the second by his wife, Kat.

The master closet and bath. Photo: Matt McCourtney
To accommodate visitors, the property includes a stand-alone, 800-square-foot, one-bedroom guest house.
Why sell? It seems Chaffee’s planning to build a new home—again from the ground up—in Lake Tahoe.
The Belvedere home, with its $29.5 million asking price, is listed with agents Lydia Sarkissian and William Bullock of Golden Gate Sotheby’s.

One of two home offices. Photo: Matt McCourtney

A second kitchen. Photo: Matt McCourtney

The den looks out to the views. Photo: Matt McCourtney

The fitness room. Photo: Matt McCourtney

Outdoor spaces abound. Photo: Matt McCourtney

The covered patio. Photo: Matt McCourtney

Another terrace, this one off the master suite. Photo: Matt McCourtney

The outdoor dining area and gardens. Photo: Matt McCourtney